As professional historians, who have done a lot of different historical walking tours before, this was simply the best we've ever experienced. Based on original archival research and extensive oral history work, Joline is able to present information and narratives that simply aren't available in published histories (yet!). I cannot recommend taking this tour highly enough. You will gain a unique perspective of life in Simon's Town and the Cape, and it's an unforgettable experience.
Simon's Town History Tour
Uncover Simon’s Town through silenced stories of slavery
The Finer Details
Just outside Cape Town, this coastal naval town is often associated with dramatic scenery, penguins at Boulders Beach, and a long maritime presence, yet beneath that familiar image lies a far more complicated story shaped by slavery, colonial expansion, and displacement.
This walk uses the history of slavery in Simon’s Town as a lens through which to understand the broader development of South Africa. As you move through the town, your Expert connects local histories to the practices of the Dutch East India Company, tracing how trade, empire, and forced labor reshaped both the coastline and the lives tied to it. What does a harbor remember long after ships have disappeared?
The experience unfolds through stories rather than spectacle. Along the route, conversations touch on early Indigenous San and Khoi history, the arrival of Dutch and later British colonial settlement, and the layered social world that emerged around the port. These histories are deeply researched, yet the experience remains approachable and grounded in human stories rather than academic distance.
The sea remains central throughout the walk. Simon’s Town developed through exchange, movement, and conflict, becoming both a naval center and a site deeply tied to the slave trade. At key locations connected to cultural exchange and colonial expansion, your Expert reveals how global systems of power shaped everyday life at the southern edge of Africa.
The tour continues at the Simon’s Town Museum, where personal histories and community memory illuminate the experiences of Cape Malay families expelled during apartheid. Their cultural legacy still shapes the town today, despite decades of forced removals and erasure. Standing in these spaces, history feels less settled and far more personal.
The experience concludes near the mosque in the old Malay Quarter, where further layers of Simon’s Town’s history come into view. By the end of the walk, you’ll leave with more than dates or historical facts. The stories encountered here linger, revealing Simon’s Town as a microcosm of slavery, apartheid, resilience, and the ongoing importance of remembering voices too often pushed aside.
Where You’ll Go
From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.
-
Simon's Town old Malay Quarter
-
Simon's Town Museum
What’s Included As Standard
Here’s a look at what your tour covers, plus anything you’ll want to consider arranging separately, so you can plan with confidence.
Included
-
English-speaking expert guideTours led in English, offering you unbroken understanding throughout.
-
Intentionally sized groupsA smaller group means more time for conversations and questions.
-
Tickets and entrance feesAll entry tickets included (unless clearly stated otherwise).
-
HeadsetsHeadsets are included on tours that need them, so every word can be heard.
Not Included
-
GratuitiesWe encourage tipping as a way to thank your guide after your experience.
-
Food and drinkRefreshments are only included during a tour when clearly noted.
-
Transportation to and from the meeting pointUnless noted, pre- and post-tour transport isn’t included - this service can be added by request.
-
Hotel pickup or drop-offUnless noted, travel to or from accommodation isn’t included - this service can be added by request.
Where You'll Explore
Make the Most of Your Tour
Some helpful advice for getting the most from your experience, from practical prep to small on-the-day tips.
Dos:
- Wear comfortable footwear
- Check the weather and dress appropriately
- Bring a bottle of water (no glass)
- Feel free to ask your Expert anything
Don'ts:
- Bring firearms or weapons
- Bring sharp objects (e.g. knives, swiss army knives, switchblades, hiking sticks)
- Dress inappropriately to enter religious sites or sacred monuments
Any questions? You can always
contact us.
Frequently Asked Questions
With the exception of the museum visit, the majority of this walk takes place outside. If it is raining, please bring an umbrella and sensible shoes. Our walks happen rain or shine.
We do not visit the penguins on our tour, although you can explore Simon’s Town at your own leisure afterward.
Simon’s Town is relatively easy to get around in a wheelchair - the streets are mostly well paved. There may be some hills on the streets leading up from the seafront.
Don’t just take our word for it
We have done many Context Tours. Your question as to whether I would recommend Context is not logical since we just brought 5 guests to this tour. We have clearly already recommended you. All of us were glad to have done this tour.
Joline had to overcome our being delayed and, one of our group of 3 had to return to Cape Town, ill. She was most accommodating, very cordial and clearly very knowledgeable. She also tried to put 100 lbs of cement into a 10 lb. bag. Too much information given our circumstances. That said, she is remarkably well informed and totally pleasing and accommodating. If anything, too much detail and not enough story-telling.
Let Your Curiosity Shape Your Journey
Join passionate experts on intimate walking tours that reveal a city’s unique stories, spark conversations, and leave you seeing the world—and yourself—a little differently.
Structured, never scripted
Your interests guide your Expert, leading to stories and perspectives that matter to you.
Crafted for conversation
With ten or fewer guests, ask questions, engage with your Expert, and fully immerse yourself.
Experts, not guides
Explore with 1,200+ Experts—from historians and architects to archaeologists and chefs.
